Recent Developments in Pd0-Catalyzed Alkene-Carboheterofunctionalization Reactions

被引:115
作者
Garlets, Zachary J. [1 ]
White, Derick R. [1 ]
Wolfe, John P. [1 ]
机构
[1] Univ Michigan, Dept Chem, 930 N Univ Ave, Ann Arbor, MI 48109 USA
关键词
alkenes; carbocycles; heterocycles; palladium; synthetic methods; ENANTIOSELECTIVE TOTAL-SYNTHESIS; PD-CATALYZED CARBOAMINATION; ASYMMETRIC TOTAL-SYNTHESIS; NATURAL-PRODUCT SYNTHESIS; STEREOCONTROLLED SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; MIGRATORY INSERTION; ALDER REACTIONS; MILD CONDITIONS; WACKER REACTION;
D O I
10.1002/ajoc.201600577
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This Focus Review summarizes recent developments in palladium-catalyzed alkene carboalkoxylation and carboamination reactions. New synthetic methods that have been reported within the past four years are described, along with mechanistic insights and the influence of reaction mechanism on product stereochemistry. The applications of these transformations to the synthesis of natural products and other biologically relevant compounds are also discussed.
引用
收藏
页码:636 / 653
页数:18
相关论文
共 109 条
[1]   Cascade Pd(II)-catalyzed Wacker lactonization-Heck reaction: rapid assembly of spiranoid lactones [J].
Albarghouti, Ghassan ;
Kotikalapudi, Ramesh ;
Lankri, David ;
Valerio, Viviana ;
Tsvelikhovsky, Dmitry .
CHEMICAL COMMUNICATIONS, 2016, 52 (15) :3095-3098
[2]   Synthesis of Substituted Tetrahydroindoloisoquinoline Derivatives via Intramolecular Pd-Catalyzed Alkene Carboamination Reactions [J].
Alicea, Jeremiah ;
Wolfe, John P. .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (09) :4212-4217
[3]  
[Anonymous], 2009, ANGEW CHE
[4]   Total synthesis of (+)-batzelladine A and (-)-batzelladine D via [4+2]-annulation of vinyl carbodiimides with N-alkyl imines [J].
Arnold, Michael A. ;
Day, Kenneth A. ;
Duron, Sergio G. ;
Gin, David Y. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (40) :13255-13260
[5]   The tethered Biginelli condensation in natural product synthesis [J].
Aron, ZD ;
Overman, LE .
CHEMICAL COMMUNICATIONS, 2004, (03) :253-265
[6]  
Babij, 2013, ANGEW CHEM, V125, P9417, DOI DOI 10.1002/ANIE.201500636
[7]  
Babij N. R., 2012, ANGEW CHEM, V124, P4204
[8]   Stereocontrolled Synthesis of Bicyclic Sulfamides via Pd-Catalyzed Alkene Carboamination Reactions. Control of 1,3-Asymmetric Induction by Manipulating Mechanistic Pathways [J].
Babij, Nicholas R. ;
McKenna, Grace M. ;
Fornwald, Ryan M. ;
Wolfe, John P. .
ORGANIC LETTERS, 2014, 16 (12) :3412-3415
[9]   Desymmetrization of meso-2,5-Diallylpyrrolidinyl Ureas through Asymmetric Palladium-Catalyzed Carboamination: Stereocontrolled Synthesis of Bicyclic Ureas [J].
Babij, Nicholas R. ;
Wolfe, John P. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (35) :9247-9250
[10]   Asymmetric Total Synthesis of (+)-Merobatzelladine B [J].
Babij, Nicholas R. ;
Wolfe, John P. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (17) :4128-4130